3 H ‐Indol‐3‐ols by a novel ring contraction | Zendy

Lednicer Daniel | Zendy; Emmert D. Edward | Zendy

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3 H ‐Indol‐3‐ols by a novel ring contraction

Author(s) -

Lednicer Daniel,

Emmert D. Edward

Publication year - 1970

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570070316

Subject(s) - chemistry , alkylation , ring (chemistry) , liquid ammonia , amide , tribromide , potassium , medicinal chemistry , contraction (grammar) , ammonia , base (topology) , stereochemistry , organic chemistry , catalysis , mathematical analysis , mathematics , medicine

Treatment of α‐hydroxy‐α‐phenyl‐ o ‐toluidide with phosphorus tribromide afforded a series of 4 H ‐3,1‐benzoxazines. These last, when reacted with potassium amide in liquid ammonia, ring contracted to 2,3‐disubstituted 3 H ‐indol‐3‐ols. The scope of this rearrangement was examined. The indolols on treatment with hot base were found to rearrange to indoxyls. Several of these as well as their N ‐alkylation products are described.

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